Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (4): 708.

• Articles • Previous Articles     Next Articles

Synthesis, Crystal Structure and Bioactivities of 2-Cyanoacrylates Containing 5-Ethoxy-1,3,4-thiadiazol-2-methylamine Moiety

WANG Ting-Ting, BING Gui-Fang, ZHANG Xin, QIN Zhen-Fang, YU Hai-Bo, QIN Xue, DAI Hong, FANG Jian-Xin*   

  1. State Key Laboratory of Elemento-Organic Chemistry, Tianjin Key Laboratory of Pesticide Science, Nankai University, Tianjin 300071, China
  • Received:2009-05-31 Online:2010-04-10 Published:2010-04-10
  • Contact: FANG Jian-Xin. E-mail: yssfjx@yahoo.com.cn
  • Supported by:

    国家自然科学基金(批准号: 20772068)资助.

Abstract:

Herbicidal activity of cyanoacrylates has been the subject of intense interest for the past decades. A detailed study revealed that cyanoacrylates are inhibitors of photosystemⅡ(PSⅡ) electron transportation. In this paper, a series of novel 2-cyanoacrylates containing 5-ethoxy-1,3,4-thiadiazol-2-methylamine moiety were synthesized from 5-ethoxy-1,3,4-thiadiazol-2-methanamine and 2-cyanoacrylates in refluxing ethanol. Their structures were confirmed by 1H NMR and elemental analysis. Biological activity tests showed that some compounds exhibited good herbicidal activities and excellent selectivity against dicotyledonous weeds such as rape and amaranth pigweed. Compound 6j show the highest herbicidal activity at the dose of 600 g/ha with 100% and 95.2% inhibition activity against rape and amaranth pigweed in postemergency treatment. It show the same herbicidal level as the contrast compound B. A appropriate size group at the 3-position of acrylates is essential for high herbicidal activity. 2-Cyanoacrylates containing 5-ethoxy-1,3,4-thiadiazol-2-methylamine moiety have the research potency, further study is underway.

Key words: 5-Ethoxy-1,3,4-thiadiazol-2-methylamine; Cyanoacrylate; Herbicidal activity

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